TW577889B - Sulfonamide compound having hypoglycemic activity or PDE-V inhibitory activity - Google Patents

Info

Publication number

TW577889B

TW577889B TW088121089A TW88121089A TW577889B TW 577889 B TW577889 B TW 577889B TW 088121089 A TW088121089 A TW 088121089A TW 88121089 A TW88121089 A TW 88121089A TW 577889 B TW577889 B TW 577889B

Authority

TW

Taiwan

Prior art keywords

methyl

pyridine

chloro

lhf

imidazo

Prior art date

1998-12-04

Links

• Espacenet
• Global Dossier
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• -1 Sulfonamide compound Chemical class 0.000 title claims abstract description 727
• 229940124530 sulfonamide Drugs 0.000 title claims abstract description 39
• 230000002401 inhibitory effect Effects 0.000 title abstract 4
• 230000002218 hypoglycaemic effect Effects 0.000 title abstract 2
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
• 201000010099 disease Diseases 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 466
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 229
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 196
• 238000011049 filling Methods 0.000 claims description 143
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 134
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 127
• 230000002079 cooperative effect Effects 0.000 claims description 65
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 50
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 31
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 30
• 150000001412 amines Chemical class 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 239000007789 gas Substances 0.000 claims description 20
• 239000000203 mixture Substances 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 125000003277 amino group Chemical group 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
• 239000011734 sodium Substances 0.000 claims description 10
• 150000007857 hydrazones Chemical class 0.000 claims description 8
• 229910052708 sodium Inorganic materials 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 229910052736 halogen Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical group 0.000 claims description 7
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 159000000000 sodium salts Chemical class 0.000 claims description 6
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 239000000460 chlorine Chemical group 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 230000002441 reversible effect Effects 0.000 claims description 3
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 235000010290 biphenyl Nutrition 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 229910052722 tritium Inorganic materials 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
• 125000001544 thienyl group Chemical group 0.000 claims 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims 3
• 206010003210 Arteriosclerosis Diseases 0.000 claims 2
• 206010006895 Cachexia Diseases 0.000 claims 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
• 206010020772 Hypertension Diseases 0.000 claims 2
• 230000002159 abnormal effect Effects 0.000 claims 2
• 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
• 206010012601 diabetes mellitus Diseases 0.000 claims 2
• 125000001188 haloalkyl group Chemical group 0.000 claims 2
• WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 claims 2
• 229960000611 pyrimethamine Drugs 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 claims 1
• SSXYKBHZZRYLLY-UHFFFAOYSA-N 2-chloro-1,3-oxazole Chemical compound ClC1=NC=CO1 SSXYKBHZZRYLLY-UHFFFAOYSA-N 0.000 claims 1
• FZESPVBONPPRAW-UHFFFAOYSA-N 2-methyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC=C2NC(C)=NC2=N1 FZESPVBONPPRAW-UHFFFAOYSA-N 0.000 claims 1
• LVISFHSWRHMNMQ-UHFFFAOYSA-N 4-benzyl-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1CC1=CC=CC=C1 LVISFHSWRHMNMQ-UHFFFAOYSA-N 0.000 claims 1
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
• 208000010412 Glaucoma Diseases 0.000 claims 1
• 208000022461 Glomerular disease Diseases 0.000 claims 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
• 206010019280 Heart failures Diseases 0.000 claims 1
• 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
• 201000001431 Hyperuricemia Diseases 0.000 claims 1
• 206010061218 Inflammation Diseases 0.000 claims 1
• 206010022489 Insulin Resistance Diseases 0.000 claims 1
• 201000005505 Measles Diseases 0.000 claims 1
• JXBSBDDXANEZQW-UHFFFAOYSA-N N-methyl-N-propyl-9H-fluoren-1-amine Chemical compound C1C2=CC=CC=C2C2=C1C(N(C)CCC)=CC=C2 JXBSBDDXANEZQW-UHFFFAOYSA-N 0.000 claims 1
• 206010028980 Neoplasm Diseases 0.000 claims 1
• 208000001132 Osteoporosis Diseases 0.000 claims 1
• 206010033645 Pancreatitis Diseases 0.000 claims 1
• 208000018262 Peripheral vascular disease Diseases 0.000 claims 1
• 206010036049 Polycystic ovaries Diseases 0.000 claims 1
• 208000001647 Renal Insufficiency Diseases 0.000 claims 1
• 206010039085 Rhinitis allergic Diseases 0.000 claims 1
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 1
• 208000006011 Stroke Diseases 0.000 claims 1
• BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 claims 1
• 230000003187 abdominal effect Effects 0.000 claims 1
• 230000005856 abnormality Effects 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 125000004423 acyloxy group Chemical group 0.000 claims 1
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
• 150000004996 alkyl benzenes Chemical group 0.000 claims 1
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
• 201000010105 allergic rhinitis Diseases 0.000 claims 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
• 230000006497 arterial abnormality Effects 0.000 claims 1
• 208000006673 asthma Diseases 0.000 claims 1
• 239000008280 blood Substances 0.000 claims 1
• 210000004369 blood Anatomy 0.000 claims 1
• XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims 1
• 201000011510 cancer Diseases 0.000 claims 1
• 230000000747 cardiac effect Effects 0.000 claims 1
• VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 230000001684 chronic effect Effects 0.000 claims 1
• 230000004069 differentiation Effects 0.000 claims 1
• 210000001339 epidermal cell Anatomy 0.000 claims 1
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
• 229960002001 ethionamide Drugs 0.000 claims 1
• 208000004104 gestational diabetes Diseases 0.000 claims 1
• 239000008103 glucose Substances 0.000 claims 1
• 230000010030 glucose lowering effect Effects 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 201000001421 hyperglycemia Diseases 0.000 claims 1
• 230000036039 immunity Effects 0.000 claims 1
• 230000001771 impaired effect Effects 0.000 claims 1
• 201000001881 impotence Diseases 0.000 claims 1
• 230000004054 inflammatory process Effects 0.000 claims 1
• 230000000968 intestinal effect Effects 0.000 claims 1
• 230000008991 intestinal motility Effects 0.000 claims 1
• 201000006370 kidney failure Diseases 0.000 claims 1
• 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
• 229940050176 methyl chloride Drugs 0.000 claims 1
• WGMSCEXSHWDIIJ-UHFFFAOYSA-N n-(butylsulfamoyl)-3-[(2-chloro-4-ethoxyphenyl)methyl]-2-methylimidazo[4,5-b]pyridine-5-carboxamide Chemical compound C12=NC(C(=O)NS(=O)(=O)NCCCC)=CC=C2N=C(C)N1CC1=CC=C(OCC)C=C1Cl WGMSCEXSHWDIIJ-UHFFFAOYSA-N 0.000 claims 1
• 201000008383 nephritis Diseases 0.000 claims 1
• RJQRCOMHVBLQIH-UHFFFAOYSA-M pentane-1-sulfonate Chemical compound CCCCCS([O-])(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-M 0.000 claims 1
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 208000002815 pulmonary hypertension Diseases 0.000 claims 1
• 208000037803 restenosis Diseases 0.000 claims 1
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 1
• 235000021286 stilbenes Nutrition 0.000 claims 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
• 229940045145 uridine Drugs 0.000 claims 1
• 206010020751 Hypersensitivity Diseases 0.000 abstract 1
• 208000026935 allergic disease Diseases 0.000 abstract 1
• 230000007815 allergy Effects 0.000 abstract 1
• 230000003182 bronchodilatating effect Effects 0.000 abstract 1
• 239000008194 pharmaceutical composition Substances 0.000 abstract 1
• 238000011321 prophylaxis Methods 0.000 abstract 1
• 230000002040 relaxant effect Effects 0.000 abstract 1
• 210000002460 smooth muscle Anatomy 0.000 abstract 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 abstract 1
• 238000011282 treatment Methods 0.000 abstract 1
• 230000000304 vasodilatating effect Effects 0.000 abstract 1
• 238000002360 preparation method Methods 0.000 description 307
• 239000013078 crystal Substances 0.000 description 230
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 102
• YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 96
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
• 239000000843 powder Substances 0.000 description 64
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
• 238000003756 stirring Methods 0.000 description 50
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 47
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
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• 239000007787 solid Substances 0.000 description 42
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• 238000005481 NMR spectroscopy Methods 0.000 description 33
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• 238000001816 cooling Methods 0.000 description 29
• 238000001914 filtration Methods 0.000 description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• 150000003456 sulfonamides Chemical class 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• 238000005160 1H NMR spectroscopy Methods 0.000 description 21
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• 235000002639 sodium chloride Nutrition 0.000 description 21
• 239000002253 acid Substances 0.000 description 20
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• 239000012044 organic layer Substances 0.000 description 18
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• 238000010438 heat treatment Methods 0.000 description 16
• 238000010898 silica gel chromatography Methods 0.000 description 16
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• 238000010992 reflux Methods 0.000 description 15
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
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• 239000002244 precipitate Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 125000004585 polycyclic heterocycle group Chemical group 0.000 description 8
• 241000196324 Embryophyta Species 0.000 description 7
• 125000005907 alkyl ester group Chemical group 0.000 description 7
• OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 7
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• VJDXFAQSGBLNFO-UHFFFAOYSA-N methyl 2-chloro-6-phenylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC=C1C1=CC=CC=C1 VJDXFAQSGBLNFO-UHFFFAOYSA-N 0.000 description 1
• SBQBPKUDXAELAZ-UHFFFAOYSA-N methyl 3,5-dichloropyridine-2-carboxylate Chemical compound COC(=O)C1=NC=C(Cl)C=C1Cl SBQBPKUDXAELAZ-UHFFFAOYSA-N 0.000 description 1
• AAVFVGCJNXARFR-UHFFFAOYSA-N methyl 3-[(2-chloro-4-iodophenyl)methyl]-2-methylimidazo[4,5-b]pyridine-5-carboxylate Chemical compound C12=NC(C(=O)OC)=CC=C2N=C(C)N1CC1=CC=C(I)C=C1Cl AAVFVGCJNXARFR-UHFFFAOYSA-N 0.000 description 1
• IAXVWRYPLBFCLH-UHFFFAOYSA-N methyl 3-[(6-chloro-1,2-dimethylbenzimidazol-5-yl)methyl]-2-methylimidazo[4,5-b]pyridine-5-carboxylate Chemical compound C12=NC(C(=O)OC)=CC=C2N=C(C)N1CC(C(=C1)Cl)=CC2=C1N(C)C(C)=N2 IAXVWRYPLBFCLH-UHFFFAOYSA-N 0.000 description 1
• JEJMDUMJSZTJTI-UHFFFAOYSA-N methyl 4,6-dichloropyridine-3-carboxylate Chemical compound COC(=O)C1=CN=C(Cl)C=C1Cl JEJMDUMJSZTJTI-UHFFFAOYSA-N 0.000 description 1
• OZDIHMBAXNOTML-UHFFFAOYSA-N methyl 4-acetamido-2-chloro-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1Cl OZDIHMBAXNOTML-UHFFFAOYSA-N 0.000 description 1
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• MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
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• QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
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• WURGAKORBPRKIL-UHFFFAOYSA-N tetrazolidine-1,2,3,4,5-pentamine Chemical compound NC1N(N)N(N)N(N)N1N WURGAKORBPRKIL-UHFFFAOYSA-N 0.000 description 1
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• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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